Reaction of dhsopropylbenzene-alpha, alpha&#39;-diol with phenolic compounds and products thereof



United States Patent Cflice 3,384,617 Patented May 21, 1968 REACTION OFDIISOPROPYLBENZENE-oL,u'-DIOL WITH PHENOLIC COMPOUNDS AND PRODUCTSTHEREOF Salvatore A. Casale, Morris Township, Morris County, Thomas M.Cawthon, Dover, and Wilbert M. Wenner, Rockaway, N.J., assignors toAllied Chemical Corporation, a corporation of New York No Drawing.Original application Apr. 30, 1962, Ser. No. 191,279, now Patent No.3,256,347, dated June 14, 1966. Divided and this application Feb. 21,1966, Ser. No. 544,051

5 Claims. (Cl. 260-47) This application is a division of application forUS. Letters Patent Ser. No. 191,279, filed Apr. 30, 1962.

This invention relates to epoxide resins and more particularly refers tonew and improved epoxide resins and process for their preparation.

Epoxide resins are one of the newest and most versatile of modernplastics. Their commercial success has been due to their outstandingchemical and mechanical properties which render them useful as surfacecoatings, industrial castings, high-strength adhesives, durablelaminates, cold solders, lightweight foams and potting compounds for allvarieties of electrical and electronical apparatus.

In order to adapt and expand their area of application, the inherentproperty of hardness must be complemented by a sufiicient degree offlexibility and elasticity. More particularly, since these epoxideresins are inherently rigid, they tend to chip and crack underindustrial conditions, thereby severely curbing their utility. In orderto overcome this basic disadvantage, epoxide resins are usually cured tothermoset condition in conjunction with various plasticizing agents.

Generally, epoxide resins prepared from relatively simple dihydroxycompounds such as resorcinol and 2,2-bis (4,4'phenylhydroxy)propane,'are readily susceptible to modification by the addition of plasticizingagents. However, where more complex compounds are employed, thisdisadvantage of incompatability with conventional plasticizers arises asa significant factor in their industrial application and success.

An object of the present invention is to provide new epoxide resinswhich possess desirable properties of hardness, durability and chemicalinertness. Another object is to provide new epoxide resins which arereadily compatible with conventional plasticizers. A further object isto provide a method for preparing new epoxide resins having improvedproperties. A still further object is to provide a method for preparingan intermediate compound for the preparation of these new epoxideresins. Other objects and advantages will be apparent from the followingdescription.

These new epoxide resins having the desirable properties of hardness,durability and chemical inertness and compatible with plasticizers, maybe prepared in accordance with the present invention by reactingdiisopropylbenzene-a,a-diol, preferably para-diisopropylbenzene-a,a'-di0l or meta-diisopropyl'benzene-a,a-diol which exhibit highreactivity, or mixtures thereof and a phenolic compound having theformula:

wherein R and R are selected from the group consisting of methyl, ethyl,methoxy, ethoxy, chloro, bromo, iodo and fluoro and m: and p areintegers ranging from 0 to 1,

preferably in a molar proportion from about 0.5 to 4 mols, desirably 0.8to 1.1 mols of phenolic compound per mol of diisopropylbenzene-a,u'-diolat a temperature Within the range of about 30 C. to 200 C. preferably C.to 150 C. in the presence of an organic solvent inert under the reactionconditions and in the presence of an acid-activated clay catalyst tocfiect reaction of the phenolic compound and thediisopropylbenzene-a,adiol to produce a p-phenol alkylated1,1,3-trimethyl-1,2- dihydroindene having the formula:

wherein R and R are selected from the group consisting of methyl, ethyl,methoxy, ethoxy, chloro, bromo, iodo and fluoro, and m. and p areintegers ranging from 0 to 1, and n is an integer ranging from O to 8,preferably 0 to 5, admixing said p-phenol alkylated 1,l,3-trimethyl-1,2-dihydroindene with a halohydrin in a molar proportion of about 1 to 15mols of h'alohydrin per mol of said p-phenol alkylated1,1,3-trimethyl-1,2-dihydroindene and maintaining said mixture in thepresence of a basic medium at a temperature within the range of about 20C. to 120 C., preferably 80 C. to C. to effect reaction of thehalohydrin and p-phenol alkylated 1,1,3-trimethyl-1,2-dihydroindene toproduce epoxy resinous reaction product.

The p-phenol alkylated 1,1,3-trimethyl-1,2-dihydroindene is a newcompound produced by reaction of diisopropylbenzenea,a-diol and aphenolic compound as illustrated by the following equation:

OH CH3 CH3 wherein n is an integer of at least 2, R and A are selectedfrom the group consisting of methyl, ethyl, methoxy, ethoxy, chloro,bromo, iodo and fluoro, 'and m and p are integers from 0 to 1.

The reactant p-diisopropylbenzene-e d-diol and m-diisopropylbenzene-w,u'-diol are white crystalline solids having meltingpoints of 141 C. and 136 C., respectively.

The reactant phenolic compound may be of the general formula heretoforerecited and of which the following compounds are illustrative: Phenol2-chlorophenol 2,6-dichlorophenol 2-methylphenol 2,6-dimethoxyphenol2-ethoxyphenol Z-bromophenol 2-methyl-6-methoxyphenol 2,6-dimethylphenol2-methyl-6-fiuorophenol 2-methoxyphenol 2,6-diethoxyphenol In order toobtain high yield of the new p-phenol alkylated1,l,3-trimethyl-1,2-dihydroindene, control of the conditions of reactionis important.

One such condition is the molar ratio of the reactants. It has beenfound that molar ratios in excess of 4 mols of phenolic compounds permol of diisopropylbenzenea,ct-diol produces a reaction product whichcontains about 50 percent or more by weight of impurities while molarratios less than about 0.5 mol of phenolic compound per mol ofdiisopropylbenzene-a,adiol produces a substantial quantity ofl,1,3-trimethyl-1,2-dihydroindene products devoid of p-phenol endgroups. Thus, molar ratios ranging from about 0.8 to 3 mols of phenoliccompound per mol of diisopropylbenzene-a,a-diol have been found toproduce optimum yields, with the molar ratios of 0.8 to 1.1 beingpreferred.

Further, it has been found that the reaction of the phenolic derivativewith dliSOpIOPYlbHZCH-Ot,0t'-dl0l will not commence to a significantdegree unless a catalyst is employed. Conventional mineral acid or Lewisacid catalyst have been found to be ineffective. In contrast,substantial yields in the order of about 70 to about 95 percent oftheoretical of the desired p-phenol alkylated 1,1,3-trimethyl-l,2-dihydroindene are readily realized when an acid-activatedsilicious material is present during the reaction. Generally speaking,an acid-activated clay consisting chiefly of silica and alumina is to bepreferred. More specifically, an acid-activated clay of thenonswellable, bentonite-type consisting of about 40 to 90 percent byweight of silica and about 3 to 20 percent of alumina, as well as smallquantities of one or more oxides of other metals such as iron,magnesium, sodium, calcium and potassium has been successfully employed.The quantity of catalyst is not critical and may vary over a wide range.Generally, up to 40 percent by weight based on the amount of thereactants is employed with the range of 5 to 20 percent being preferred.

A silicious material in the form of a porous clay may be acid-activatedby any suitable procedure. For example, a slurry of 1 part by weight ofclay to parts by weight of 5 percent mineral acid solution may be boiledfor a period of 1 hour. The excess spent acid may then be separated fromthe clay, first by settling and decantation followed by wringing of thewet clay. The resulting acidactivated silicious material may then bedried to a powder in a flash drier.

Another factor is the requirement of a suitable solvent during thereaction for the resulting p-phenol alkylated1,1,3-trimethyl-1,2-dihydroindene. If a solvent is absent, the reactiondoes not proceed as desired. The amount of solvent may vary over aconsiderable range and in practice an organic solvent employed in theamount of about 50 to 200 percent by weight based upon the amount of thereactants has been found satisfactory. Normally, organic solvents whichare inert under the conditions of the reaction and which dissolvep-phenol alkylated 1,1,3- trimethyl-1,2-dihydroindene are suitable.Illustrative examples of suitable solvents are benzene, toluene, xylene,sym-tetrachloroethane, cyclohexane and the like.

Although reaction temperatures in the range from about 30 C. to about200 C. may be employed, it has been found that optimum yields of highestpurity are secured when reaction temperatures of about 80 C. to about150 C. are utilized.

In preferred operation, the diisopropylbenzenea diol and phenolicreactants are admixed and heated in the presence of an acid-activatedsilicious material and an organic solvent to a temperature of about C.to C. for a period of about 1 hour. The reaction mixture is filtered toremove the acid-activated silicious material. Isolation is effected bythe addition of water to the reaction mixture and organic solventremoved by azeotropic distillation followed by filtration of theinsoluble p-phenol alkylated 1,l,3-trimethyl-1,2-dihydroindene from theremaining aqueous phase. Any impurities in the form of1,4-bis(p-hydroxycumyl)benzene may be disposed of by the addition of asuitable solvent such as carbon tetrachloride followed by isolation ofthe purified p-phenol alkylated 1,1,3-trimethyl-1,2-dihydroindene byfiltration and conventional drying procedures.

The next step in the reaction is the production of p-phenol alkylated1,1,3-trimethyl-1,2-dihydroindene with a halohydrin. The halohydrins arewell known compounds and may be generally described as hydrocarboncompounds in which a halogen is attached to a carbon atom and whichcontain an epoxide group or have a hydroxyl group attached to the carbonatom adjacent to the carbon atom to which is attached a halogen. Thehalohydrins as exemplified by the haloepoxide type compound have thegeneral formula:

wherein R and R are hydrogen or an organic radical having 1 to 5 carbonatoms containing only inert sub stituents, and X is a halogen.

The halohydrins which contain a hydroxyl group may be exemplified by theformula:

wherein R and R are hydrogen or an organic radical having 1 to 5 carbonatoms containing only inert substituents, X is a halogen and Y and Z arehalogens or hydroxyls, such that Y is halogen when Z is hydroxyl andconversely. These halohydrins may also be successfully employed sinceunder the conditions of reaction they convert, in situ, into compoundshaving an epihalo structure. Illustrative examples of the reactanthalohydrins are as follows: 1-chloro-2,3-epoxypropane1-chloro-2,3-epoxybutane 1-chloro-2,3-epoxypentanel-chloro-2,3-epoxyhexane 1-bromo-2,3-epoxypropanel-bromo-2,3-epoxybutane 1-bromo-2,3-epoxypentane 1-bromo-2,3-epoxyhexane1,3-dichloro-2-propanol 1,3-dibromo-2-propanol 1,2-dichloro-3-propanol1,2-dibrorno-3-propanol 1,3-dichloro-2-butanol 1,3-dibromo-2-butanol3,5-dichloro-4-hexanol 3,5-dibromo-4-hexanol The physical and mechanicalproperties of the resulting epoxide resin may be regulated to satisfythe demand of the anticipated application by varying the molar ratio ofthe reactants and in general a range of 1 to 15 mols halohydrin top-phenol alkylated 1,l,3-trimethyl-l,2-dihydroindene give productsuseful for commercial application. Regulation of the molar ratio of thereactants directly effects the resulting molecular Weight of the epoxideresin. For example, when molar ratios of about 8 mols of halohydrin permol of p-phenol alkylated 1,1,3-trimethyl-1,2-dihydroindene are employedepoxide resins having molecular weight of about 500 to 800 are securedas compared to molecular weights of about 7000 to 10,000 when molarratios of about 3:1 are utilized.

Generally, the alkali is utilized in excess of its stoichiometric amountof 2 mols alkali per mol p-phenol alkylated1,1,3-trimethyl-1,2-dihydroindene. Conventional means of molecularweight regulation such as growth-inhibitors and chain terminators mayalso be employed if desired. Reaction temperatures in the range of about70 to 120 with the preferred being 80 to 105 C. have been found to giveexcellent yields. It is understood that higher or lower reactiontemperature may also be successfully employed with an inverse variationof reaction time. Also, use of inert organic solvents such as benzene,toluene, xylene may be utilized although the presence of such solventstend to inhibit the rate of polymerization due to dilution.

These new epoxide resins prepared from the reaction of p-phenolalkylated 1,1,3-trimethyl-1,2-dihydroindene and a halohydrin derivativemay be cured to thermoset condition by the addition of conventionalcuring agents such as diethylenetriamine, phenylenediamine, phthalicanhydride. If a greater degree of elasticity or flexibility is desired,the epoxide resin is further treated with conventional plasticizingagents. Such plasticizing procedures may be employed in conjunction withcuring or modifying agents or, if desired, at a time subsequent.Heretofore many epoxide resins were unable to be modified sinceconventional plasticizers such as dioctyl phthalate, dioctyl adipate,tricresyl phosphate when added to epoxide resins, tended to separatefrom the resin during curing and/or subsequent aging procedures. Asillustrated in the examples hereinbelow described, the novel epoxideresin prepared from p-phenol alkylated 1,1,3-trimethyl-1,2-dihydroindeneis readily compatible with these aforementioned impurities separated andwere removed by filtration. The filtrate was distilled in order toremove the remaining carbon tetrachloride and 37.6 parts of a fusedsolid identified as p-phenol alkylated tetramer of 1,1,3-trimethyl-1,2-dihydroindene was obtained. This corresponded to a yield of 85.5percent.

An infrared spectra analysis was conducted and indicated the presence ofabsorption bands at 12.09 and 11.32 microns which affirm the presence of1,1,4-tri-substituted benzene rings as are present in the subjectp-phenol alkylated 1,1,3 trimethyl-1,2-dihydroindene. In addition,absorption bands at 7.30 and 7.35 microns showed the presence of a gemdirnethyl group substituted on the cyclic saturated five-membered ring.Further, the presence of strong absorption bands 2.99 and 8.20 micronsshowed the presence of phenolic hydroxide groups. Elemental analysisindicated 85.9 percent carbon and 8.38 percent hydrogen as compared tothe theoretical of 87.8 carbon and 8.19 percent hydrogen. Potentiometrictitration of the phenolic hydroxide groups showed 4.22 percent phenolichydroxide groups as compared to the theoretical of 4.15 percent. Inaddition, the molecular weight of the aboveidentified compound was foundto be 880 as compared to the theoretical value of 820. The isolatedp-phenol alkylated 1,1,3-trimethyl-1,2-dihydroindene exhibited asoftening point in the range of 90 to 105 C. and an inherent viscosityof 0.03 at C. in a 5 percent by weight benzene solution.

In Table I, analogous procedures to that of Example 1 were employed andthe data obtained therefrom are tabulated hereinbelow:

1 Metadiisopropylbenzene-m,a-dinl.

plasticizing agents and greatly improved their physical and mechanicalproperties.

Examples 1 to 6 illustrate the preparation of the novel p-phenolalkylated 1,1,3-trimethyl-1,2-dihydroindene, while examples 6 to 10illustrate its conversion to the corresponding epoxide resin. In theexamples parts are by weight.

EXAMPLE 1 A reaction vessel equipped with a mechanical stirrer wascharged with 36.9 parts of p-diisopropylbenzene a,a'- diol and 15 partsof phenol in the presence of 60 parts of benzene as solvent. 6 parts ofan acid-activated clay catalyst were added (analysis: silica 87 percent;alumina 13 percent; pore diameter 200 A.; surface area, 300-600 squaremeters per gram). The reaction mixture was then heated to temperature of80 C. for a period of 8 hours at the end of which period the temperatureof the reaction mixture was decreased to 25 C. and the acid-activatedclay catalyst was removed by filtration. The residue was washed with 30parts of benzene and the resulting filtrate was combined with thefiltrate previously obtained from the removal of the catalyst clay.

To these combined filtrates, 250 parts of water were added in order toeffect azeotropic distillation of the benzene at 69.5 C. 44 parts ofcrude p-phenol alkylated 1,1,3-trimethyl-1,2-dihydroindene were isolatedfrom the remaining aqueous phase by filtration. Upon being pulverizedand dried, it was admixed with 150 parts of carbon tetrachloride attemperatrue of 77 C. for a period of 15 minutes in order to remove anyimpurities. The resulting solution was cooled to room temperature andpermitted to stand for 12 hours during which period 6.4 parts of Thefollowing examples are given to illustrate the conversion of p-phenolalkylated 1,1,3-trimethyl-1,Z-dihydroindene to its corresponding epoxideresin.

EXAMPLE 7 Into a reaction vessel equipped with reflux condenser,thermowell, mechanical stirrer and an reagent feed-opening, a charge of30.24 parts of p-phenol alkylated 1,1,3- trimethyl-1,2-dihydroindene wasadmixed with 33.3 parts of epichlorohydrin and 1 part water. Thereaction mixture was stirred and heated to temperature of C. for aperiod of 1 hour, whereupon 1.26 parts of sodium hydroxide were added.The reaction mixture was continuously agitated for an additional 15minutes, cooled to about 75 C. and an additional quantity of 1.26 partsof sodium hydroxide were added. Two similar additions of sodiumhydroxide were made at 15 minute intervals until a total of 5.04 partsof alkali has been added. The reaction mixture was then heated totemperature of C. for a period of 30 minutes. Unreacted epichlorohydrinand water were stripped from the reaction mixture by vacuum distillationat temperature of C. under 35 millimeters Hg pressure. The crude epoxideresin produced from the p-phenol alkylated 1,1,3-trimethyl-dihydroindenewas dissolved with 47.5 parts of acetone and filtered in order to removethe salt-of-reaction from the system. Isolation of the epoxide resin wasattained by removal of acetone by vacuum distillation at 130 C. under 35millimeters Hg pressure. A yield of 73 percent of opaque solid resinidentified as the epoxide resin of p-phenol alkylated 1,1,3-trimethyl-1,2-dihydroindene was obtained which possessed a molecular weightof 994, a softening point of 107 C.

\ and a relative viscosity of 1.08 in a 2 percent by weight 7 EXAMPLE 8The procedure of Example 7 was repeated employing a charge of 50.4 partsof p-phenol alkylated 1,1,3-trimethyl-1,Z-dihydroindene, 277.5 parts ofepichlorohydrin and 2.3 parts of water. To the reaction mixture wereadded a total of 9.2 parts of sodium hydroxide in 4 equal increments at15 minute intervals. A solid clear epoxide resin was obtained in theyield of 82 percent of theoretical. The epoxide resin prepared fromp-phenol alkylated 1,1,3-trimethyl-1,2-dihydroindene possessed amolecular weight of 832, softening point of 84 C. and a relativeviscosity of 1.08 in a 2 percent by weight dioxane solution.

The resin produced by Examples 7 and 8 were alternatively plasticized bythe addition of 15 percent by weight of Beetle 2168 and a 10 percent byweight addition of dibutylphthalate. Beetle 2168 is a plasticizerproduced by the American Cyanamide Company and is composed ofurea-formaldehyde resins. Detailed analytical data regarding thisplasticizer may be found in Handbook of Material Trade Names, Zimmermanand Lavine, page 80 (1953). The plasticized material was cured tothermoset condition by the addition of diethylenetriamine followed bybaking at temperature of 93 C. for a period of 45 minutes. The resultsobtained are given in Table II set forth hereinbelow:

TABLE II Physical Properties 8 1,1,3-trimethyl-1,2-dihydroindene, 83.45parts of epichlorohydrin and 1.36 parts water. Once again, 4.41 parts ofsodium hydroxide were added in 4 equal increments at 15 minuteintervals. The reaction mixture was heated to temperature of 95 C. for 2hours at the end wherein R and R are selected from the group consistingChemical Properties Rocker Tape Mau- Impact wt. 5% wt.

hardtest drel test Water acetic sodium ness test acid hydroxide Resin:

No plasticizer s. 100 Fmlei- Failed.. No effect. No effect. No effect.216-8 Beetle plastic 76 ..do Passed..- Passed do do Do. 10% Dibutylphtlmlate 82 0 do do do D0.

The above Rocker Hardness and Impact Tests are described in OrganicCoating Technology, I. Wiley & Sons, pages 642-647 (1959). The MandrelTest is described in the American Society for Testing Materials Manual,Test D522-41. The Tape Test was determined by making a V-shaped cut inthe film pressing a strip of cellophane tape over the V and abruptlyripping away the tape, followed by an examination of the cellophane tapefor any film adherence. The chemical properties of inertness to theabove-recited solutions were made on films having thicknesses of 2.5mils and employing a contact-time period of 24 hours.

As indicated by the data contained in Table II the subject epoxide resinalthough having sufiicient hardness failed to pass either the Mandrel orImpact Test, thereby evidencing a high rigidity which is readilysubjected to chipping and cracking. In contrast the epoxide resinplasticized with conventional agents maintained sufficient hardness andpossessed a substantial degree of flexibility and elasticity asindicated by the Mandrel and Impact Tests.

EXAMPLE 9 The process of Example 7 was repeated employing a reactioncharge consisting of 22.68 parts of p-phenol alkylated1,1,3-trimethyl-1,2-dihydroindene, 41.62 parts of epichlorohydrin and0.42 part water. The reaction mixture was maintained at temperature of95 C. for

parts alkali were added in 4 equal increments at 15 minute intervals.After the crude epoxide resin was purified as in Example 1, an 83percent yield of epoxide resin was obtained having a molecular weight of836, a softening point of 88 C. and a relative viscosity of 1.08 in a 2percent by weight dioxane solution.

EXAMPLE 10 A process employed in Example 7 was repeated with a reactionchar e of 22.68 parts of p-phenol alkylated of methyl, ethyl, methoxy,ethoxy, chloro, 'bromo, iodo and fiuoro and m and 12 represent theintegers 0 and 1,

40 in a molar proportion from about 0.5 to 4 mols phenolic p-phenolalkylated 1,1,3-tri1nethyl-1,2-dihydroindene having the formula:

CH3 CH3 CH3 CH3 1 ()H OH wherein R and R are selected from the groupconsisting of methyl, ethyl, methoxy, ethoxy, chloro, bromo, iodo andfiuoro and m and 2 represent the integers 0 and 1 and n represents aninteger from 0 to 8 inclusive, admixing said p-phenol alkylated 1,1,3trimethyl 1,2 dihydroindene with a halohydrin in a molar proportion ofabout 1-15 mols of halohydrin selected from the group a ppriod of 1 hourduring which mm a total of 378 consisting of an epihalohydrin and adihalohydrin in which at least one halogen atom is attached to a carbonatom alpha to the hydroxy-substituted carbon atom and the two halogenatoms are attached to different carbon atoms per mol of said p-phenolalkylated 1,1,3-trimethyl- 1,2-dihydroindene and maintaining saidmixture in the presence of a basic medium at a temperature within therange of about 20 C. to 120 C. to effect reaction of the halohydrin andp-phenol alkylated 1,1,3-trirnethyl- 1,2-dihydroindene to produce epoxyresinous reaction product.

2. A process for the production of epoxide resins which comprisesreacting diisopropylbenzene-a,a'-diol with a phenolic compound havingthe formula:

wherein R and R are selected from the group consisting of methyl, ethyl,methoxy, ethoxy, chloro, bromo, iodo and fluoro and m: and p representthe integers and 1, in a molar proportion from about 0.8 to 1.1 molsphenolic compound per mol of diisopr-opylbenzene-u,a'-dio1 at atemperature within the range of about 80 C. to 150 C. in the presence ofan inert organic solvent and in the presence of an acid-activatedsilicious catalyst to produce p-phenol alkylated 1,1,3-trimethyl1,2-dihydro indene having the formula:

wherein R and R are selected from the group consisting of methyl, ethyl,methoxy, ethoxy, chloro, bromo, iodo and fluoro and m and p representthe integers 0 and 1 and n represents an integer from 0 to 5 inclusive,admixing said p-phenol alkylated 1,1,3-trimethyl=1,Z-dihydroindene witha halohydrin selected from the group consisting of an epihalohydrin anda dih-alohydrin in which at least one halogen atom is attached to acarbon atom alpha to the hydroXy-substituted carbon atom and the twohalogen atoms are attached to different carbon atoms in a molarproportion of about 1-15 mols of halohydrin per mol of said p-phenolalkylated 1,l,3-trimethyl-1,2- dihydroindene and maintaining saidmixture in the presence of a basic medium at a temperature with therange 10 of about to C. to effect reaction of the halohydrin andp-phenol alkylated 1,1,3-trimethyl-l,2-dihydroindene to produce epoxyresinous reaction product.

3. A process as claimed in claim 2 wherein thediisopropylbenzene-u,a-diol is par-a-diisopropyl=benzene-a,u'- diol.

4. A process as claimed in claim 2 wherein thediis-opropylbenzene-u,ot'-diol is meta-diisopropylbenzene-a,adiol.

5. An epoxide resin which is a reaction product of a halohydrin selectedfrom the group consisting of an epihalohydrin and a di-halohydrin inwhich at least one halogen atom is attached to a carbon atom alpha tothe hydroxy-subs'tituted carbon atom and the two halogen atoms areattached to different carbon atoms and p-phenol alkylated 1,1,3trimethyl 1,2 di'hydroindene having the formula:

wherein R and R are selected from the group consisting of methyl, ethyl,methoxy, ethoxy, chloro, bromo, iodo and fluoro and m and p representthe integers 0 and 1 and n represents an integer from 0 to 8, saidreaction being carried out in a basic medium at a temperature of about20 to C., employing 1 to 15 mols of said halohydrin per mol of saidp-phenol alkylated 1,1,3-trimethyl-l,Z-dihydroindene.

References Cited UNITED STATES PATENTS 3,256,347 6/1966 Casale et a1.260-47 WILLIAM H. SHORT, Primary Examiner.

T. D. KERWIN, Assistant Examiner.

5. AN EPOXIDE RESIN WHICH IS A REACTION PRODUCT OF A HALOHYDRIN SELECTED FROM THE GROUP CONSISTING OF AN EPIHALOHYDRIN AND A DIHALOHYDRIN IN WHICH AT LEAST ONE HALOGEN ATOM IS ATTACHED TO A CARBON ATOM ALPHA TO THE HYDROXY-SUBSTITUTED CARBON ATOM AND THE TWO HALOGEN ATOMS ARE ATTACHED TO DIFFERENT CARBON ATOMS AND P-PHENOL ALKYLATED 1,1,3-TRIMETHYL-1,2-DIHYDROINDENE HAVING THE FORMULA: 